Sodium Hydroxide → HCID 11202571, compound

HRID 1242352Notes

Reaction equation

HRID 1242352 reaction equation
C([O:3][C:4](=[O:37])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[C:18]([CH:33]3[CH2:35][CH2:34]3)=[N:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)=[N:21][CH:22]=2)=[CH:11][C:10]=1[CH3:36])([CH3:7])[CH3:6])C.[OH-].[Na+]>C1COCC1.CCO>[CH:33]1([C:18]2[C:17]([CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:37])=[O:3])=[C:10]([CH3:36])[CH:11]=3)=[CH:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:32])[F:30])[CH:24]=3)[N:19]=2)[CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67072014HCID 67072014, compound

Product 1

HCID 11202571HCID 11202571, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.240 g (0.466 mmol) of the above prepared 2-{4-[4-cyclopropyl-2-(3-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester was dissolved in 2.8 ml of THF/EtOH=1/1, treated with 1.40 ml (3 eq.) of 1N NaOH and kept at ambient temperature for 7 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the aqueous phase extracted again with AcOEt; the combined organic layers were washed with water, dried over sodium sulfate, and evaporated to dryness. Recrystallisation from AcOEt/hexane afforded finally 0.196 g of the title compound as white solid of mp. 175–176° C.

Workup

  1. additionThe reaction mixture was then poured
  2. extractionthe aqueous phase extracted again with AcOEt
  3. washthe combined organic layers were washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customRecrystallisation from AcOEt/hexane

Sources & evidence

ORD record
ord-36d3e8d8ae7044c8851e4bb8d6ec6e4f
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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